A native of the South who often poked fun at his own weight, May first hit the national stage in 2003 as a contestant on the first season of NBC’s reality competition Last Comic Standing, which pitted aspiring stand-up comedians against each other in hopes of winning a cash prize and talent deal. He finished second, behind eventual winner Dat Phan.

He followed that up with an appearance on The Tonight Show With Jay Leno and later filmed a series of Comedy Central stand-up specials. In 2015, May released a pair of stand-up specials on Netflix: Unruly and Imperfectly Yours. He also provided the voice of Pnut on Adult Swim’s Squidbillies and appeared in an episode of Inside Amy Schumer that aired last year.